Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 19, Pages 4785-4789Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201706036
Keywords
azomethine ylide; carbene ligands; dimerization; homogeneous catalysis; metathesis
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Funding
- National Science Centre (Poland) [DEC-2012/04/A/ST5/00594]
- European Union from the European Regional Development Fund under the Operational Programme Innovative Economy
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The dimerization of a saturated N-heterocyclic carbene (NHC) to tricyclic piperazine in preference to the commonly observed Wanzlick dimerization is presented. Mechanistic investigations revealed that the N-fluorene substituent of the heterocycle is implicated in both ring opening of corresponding carbene dimer and tautomerization of NHC to an azomethine ylide. This has consequences for the fate of the NHC when generated from either an azolinium salt or a pentafluorophenyl adduct. The insights gained permitted the synthesis of a new indenylidene metathesis precatalyst, which exhibits exceptional selectivity and high TONS in self-metathesis of 1-octene.
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